Ammonium Acetate → 5-[3-(1-Aminoethyl)-5-chloro-2-methoxy-6-methylphenyl]-N,N-dimethylpyrimidin-2-amine

HRID 510869Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH3:22])=[C:4]([C:13]2[CH:14]=[N:15][C:16]([N:19]([CH3:21])[CH3:20])=[N:17][CH:18]=2)[C:5]([O:11][CH3:12])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+]>CO.C(#N)C>[NH2:29][CH:8]([C:6]1[C:5]([O:11][CH3:12])=[C:4]([C:13]2[CH:14]=[N:15][C:16]([N:19]([CH3:21])[CH3:20])=[N:17][CH:18]=2)[C:3]([CH3:22])=[C:2]([Cl:1])[CH:7]=1)[CH3:9]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-{5-chloro-3-[2-(dimethylamino)pyrimidin-5-yl]-2-methoxy-4-methylphenyl}ethanone (60 mg, 0.2 mmol), ammonium acetate (150 mg, 1.9 mmol) and sodium cyanoborohydride (24 mg, 0.38 mmol) in methanol (0.7 mL) and acetonitrile (0.7 mL) was heated at 65° C. overnight in a sealed tube. The mixture was cooled to room temperature, quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The crude product was used directly in next step (60 mg, 100%). LCMS calculated for C16H22ClN4O (M+H)+: m/z=321.1. found: 321.1.

Workup

temperatureThe mixture was cooled to room temperature
customquenched with saturated sodium bicarbonate
extractionextracted with ethyl acetate
dry with materialThe combined extracts were dried over magnesium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-207d05230796468e886e029d4b9e157b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096600B2

Reaction notes

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